Nov
4
Australian Wine Tasting + Pairings
Join us at Leo for a special night celebrating the rich and diverse wines of Australia. From the vibrant whites of the Adelaide Hills to the deep reds of the Barossa Valley, each pour has been thoughtfully selected to showcase the best of Australia’s wine regions.
Every wine will be perfectly paired with bites created by Chef Matt and his team — a menu designed to enhance and elevate each tasting with seasonal ingredients and bold, elegant flavors.
Wines:
Pikes, Hills and Valleys Riesling
Madfish, Sauvignon Blanc/Semillon
Vasse Felix, Fillus Cabernet Sauvignon
Yalumba, Samuel's Collection Shiraz
Oct
19
Grunge Brunch
Join us at Leo for a special brunch event featuring live music inspired by 90s grunge, alternative, and rock. Enjoy performances by our own Brendan Kilroy and Tina Roberts, who will be playing music from all the iconic artists.We’ll be serving our full lunch menu alongside a selection of brunch specials created just for the occasion. A variety of brunch cocktails will also be available.Reservations are required.We look forward to welcoming you for an afternoon of great food and music!
Oct
18
Annapolis Pride Parade
The BEST place to watch the Annapolis Pride parade! Leo will open at 9am, serving brunch favorites and cocktails. For all information on the Parade and Festival, visit HERE.
Aug
27
Mom's Day Out- Back To School Lunch
Celebrate the start of school with a well-deserved Moms Day Out lunch at Leo Restaurant! Enjoy some amazing music from DJ Crawdads, sip on refreshing cocktails from our specialty Spritz menu, and treat yourself to custom pieces at the permanent jewelry station by In The Sand. Plus, treat yourself exclusive perks and discounts from inspiring locally owned, women-led businesses. It’s your day to relax, connect, and celebrate—you’ve earned it!
Aug
5
Boyd Cru Wine Event: A Flight And A Bite
Join us at Leo as we celebrate local winemakers, Boyd Cru Wines with a special Flight and Bite! We’re serving up a curated wine flight paired with a tasty bite from Chef Matthew Lego—all designed to bring out the best in each pour. Discover the stories behind the wines and enjoy a relaxed, flavorful evening celebrating local craftsmanship.
Jul
3
4th of July Picnic Pack
Skip the grill and let Leo Restaurant handle your July 4th spread! Our 4th of July Picnic Pack is packed with festive favorites, made fresh and ready for easy pickup. Whether you're hosting a backyard bash or heading out on the water, we’ve got everything you need for a delicious, no-stress celebration. Each pack feeds 5-7 hungry guests and includes:Maryland Crab Soup12 Pulled Pork Sliders with Buns and Alabama White SauceRoasted Beet DipMarinated Tomato SaladSummertime PicklesFor pickup only on Thursday, July 3rd, between 2pm and 5pm. If you would like to request an earlier or later pickup time that day, please email: info@leoannapolis.com. Substitutions will not be available with this offer.
Jun
25
Seasons Wine Pairing
Join us for a Spanish-themed wine tasting experience featuring our neighbors at Seasons olive oils and vinegar. Chef Matt and his team have created a themed menu of five pairings with bold and rich flavors, perfect for enjoying with wines from all over Spain. Seasons owner, Soraya Aguilar will be with us to talk about her family's beautiful story and how her exquisite products are made.This is a 21+ event.
Jun
12
Meet The Artist- Jeff Huntington for Annapolis Arts Week
In conjunction with Annapolis Arts Week, we are excited to be a part of BOUNCE Gallery Walk! Jeff Huntington will be painting an original mursl on the excterior of Leo and hanging out after for drinks and conversation. To see all the participating businesses on the walk, visit: https://www.annapolisartsweek.com/events/gallery-walk
Jun
1
Drag Brunch w/Annapolis Pride
Celebrate Pride with a Drag Brunch featuring Queen Jalah Nicole and friends. This is a ticketed event, please visit HERE to reserve a spot.
May
31
Pride Parade Day
Celebrate Pride in Annapolis at Leo on parade day! We will be opening early at 11am for lunch, serving up Pride-themed cocktails, and we're the best place to watch the parade go by on West Street. Walk-ins welcome, reservations recommended.
Click HERE to reserve your spot. 
May
3
Catfish Cookoff
Taste delicious catfish dishes from local restaurants, judged by photographer Jay Fleming, Chef John Shields & Kevin Atticks, MD Secretary of Agriculture! Enjoy live music, cooking demos, fish-cutting demos, and a lecture from a fisheries scientist on invasive species. The Chesapeake Catfish Cook-off isn’t just an event—it’s a movement.